3-Epigibberellin A1

Base Information

• Chemical Name: 3-Epigibberellin A1
• CAS No.: 1166-98-9
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396
• DSSTox Substance ID: DTXSID401109974
• Nikkaji Number: J568.023I
• Wikidata: Q105130808
• Mol file: 1166-98-9.mol

Synonyms:3-Epigibberellin A1;Pseudogibberellin A1;3-epiGA1;3-epi-Gibberellin A1;CHEBI:142124;DTXSID401109974;1166-98-9;(1R,2R,5S,8S,9S,10R,11S,12R)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid;(1S,2R,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;(1S,2R,4aR,4bR,7S,9aS,10S,10aR)-2,7-dihydroxy-1-methyl-8-methylidene-13-oxododecahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylic acid;Gibbane-1,10-dicarboxylic acid, 2,4a,7-trihydroxy-1-methyl-8-methylene-, 1,4a-lactone, (1alpha,2alpha,4aalpha,4bbeta,10beta)-

Chemical Property of 3-Epigibberellin A1

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 348.15728848
• Heavy Atom Count: 25
• Complexity: 731

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(CCC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)O
• Isomeric SMILES: C[C@@]12[C@@H](CC[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O

Technology Process of 3-Epigibberellin A1

There total 11 articles about 3-Epigibberellin A1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

C23H32O8 (144708-78-1) → (+/-)-gibberellin A1 (545-97-1,1166-98-9,10449-51-1,75801-06-8,130610-22-9)

Guidance literature:

With methanol; DOWEX-50W-X₂; for 6h; Heating;

DOI:10.1080/00397919208021548

Reference yield:

C26H42O6Si2 (23259-61-2) → (+/-)-gibberellin A1 (545-97-1,1166-98-9,10449-51-1,75801-06-8,130610-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: n-PrSLi / dimethylformamide / 2 h / 20 °C

2: acid

With lithium n-propylmercaptide; In N,N-dimethyl-formamide;

DOI:10.1021/ja00541a071

Reference yield:

C19H24O7 (75759-20-5,79936-45-1,79936-46-2,79981-75-2) → (+/-)-gibberellin A1 (545-97-1,1166-98-9,10449-51-1,75801-06-8,130610-22-9)

Guidance literature:

Multi-step reaction with 4 steps

1: i-Pr₂NEt

2: KO-t-BU, t-BuOH / tetrahydrofuran / 0.33 h / 20 °C

3: n-PrSLi / dimethylformamide / 2 h / 20 °C

4: acid

With potassium tert-butylate; lithium n-propylmercaptide; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00541a071

upstream raw materials:

gibberellin A₁ methyl ester

tetrachloromethane

water

C₂₃H₃₂O₈

Refernces

• 1、 Voigt,Adam,Kobrina,et al.. "The giberellin series: preparation of 3-epigiberellin A3". . p. 372 - 374. Retrieved 2007/10/11.